Imidazole → 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 506641ノート

反応式

HRID 506641 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].N1[CH:26]=[CH:25]N=C1.[Cl-].[NH4+]>CN(C)C=O>[CH2:25]([O:12][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([O:1][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20])=[CH:10][CH:9]=2)=[O:13])[CH3:26]

参加物

6

反応物 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 889585-Hydroxyindole-2-carboxylic acid

生成物 1

HCID 226767305-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester収率 98.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To the solution of 10.0 g (49.0 mmol) 5-hydroxyindole-2-carboxylic acid (commercially available) in 30 ml N,N-dimethylformamide, 7.7 g (51.1 mmol) tert-butyldimethylchlorosilane and 3.5 g (51.4 mmol.) imidazole was added. After 1 hour, the solution was poured on 10% aqueous ammonium chloride solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2 v/v) as eluant to give 15.3 g (98.5%) of the compound as a white solid.

後処理

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2 v/v) as eluant

出典と根拠

ORDレコード
ord-15dc94ec6bab4687b98ddb49bb8a8b64
出典データセット
uspto-grants-2010_08
特許番号
US07786109B2

反応ノート

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